


Princess wants more

by Cagedandfree



Series: Good boys for Dean [5]
Category: Supernatural
Genre: Anal Fingering, Anal Plug, Anal Sex, Cock Cages, Crossdressing, Crossdressing Sam Winchester, Cum Eating, Daddy Issues, Daddy Kink, Dom/sub, Feminization, Finger Sucking, Inflation, M/M, Panty Kink, Pregnancy Kink, Watersports, enema inflation, i'll add more later, piss drinking
Language: English
Status: Completed
Published: 2018-01-25
Updated: 2018-01-30
Packaged: 2019-03-09 12:08:21
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 4
Words: 1,965
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/13481178
Author URL: https://archiveofourown.org/users/Cagedandfree/pseuds/Cagedandfree
Summary: The boys take it up a notch.If you don't like, don't read.





	1. Chapter 1

**Author's Note:**

> I know I never gave a time period. But let's say after season 8 and the trials.

Sam was so excited to be a pretty girl again. Unfortunately there was a case, but it was in town. The boys stopped to get coffee and there was a pregnant woman there. Sam couldn’t take his eyes off of her. Castiel and Dean defiantly noticed. When they got back to the bunker, Sam stood there naked wearing the cock cage.

“Daddy, you said not to put the plug in yet?” Sam said.

“That’s right princess. We want to do something special for you. Mommy and daddy noticed that you were looking at the pregnant girl.” Dean said.

“Yes, she looked so pretty.”

“Yeah?” Castiel smiled, running a hand through Sam’s hair. “Do you want to look like that, baby girl?”

“Do you want to be pretty and pregnant?” Dean asked.

“I can’t daddy. I’m not really a girl” Sam blushed.

“Inflation sweetie. We will give you an enema inflation, get your belly all nice and swollen.” Castiel explained.

“You would do that for me?” Sam whimpered and the boys nodded, wrapping him in a hug. 

The boys got Sam into the bathroom. Dean placed the nipple pumps on and started to get his hair in bows. Castiel put latex gloves on and attached a nozzle to the shower hose. Dean held Sam while Castiel lubed up Sam’s hole and opened him a bit and lubing up the nozzle, pushing it in. 

“Deep breaths, baby girl” Castiel said and he turned the hose on.

That water started to flow and Sam let out a sob. Dean held him tight and Castiel rubbed a hand up and down Sam’s back. Castiel placed a hand on Sam’s stomach. 

“That’s getting nice and swollen.” Castiel smiled.

“Only a few more seconds, sweetheart.” Dean praised Sam.

Castiel shut the water off and pulled the nozzle out and slid the plug in. Castiel took the gloves off and the boys helped him over to the bench and Castiel took the pumps off and placed the sheer bra on Sam. Dean got Sam in his panties, stockings and heels. Castiel slipped the satin elbow length gloves on and the boys brought him to the bedroom and Dean put make up on. Sam rubbed a hand on his swollen stomach.

“I’m fucked up. This is fucked up.” Sam whispered and Castiel started to massage his shoulders. Dean knelt in front of his brother and kissed Sam’s stomach a few times.

“You look beautiful princess.” Dean whispered looking up at his brother. “Such a pretty girl for us.” 

“You had a hard life, baby girl. If this is what you need, then it is not fucked up. It is amazing.” Castiel said. Dean stroked Sam’s stomach and kissed it.

“Princess, do you think you could dance for daddy?” Dean went back to placing open mouth kisses on his stomach while Castiel sucked on Sam’s pulse point on his neck. 

“Ye-Yes, daddy. Please. Let me dance and be pretty.” Sam moaned. 

Castiel and Dean pulled up chairs and Sam stood up starting to dance. He rubbed hand over his stomach and down his face. 

“You like that princess? You swollen stomach, you look so pretty.” Dean praised. 

“Yes, daddy. I’m a pretty princess. A pretty, pregnant princess.” Sam said.


	2. Chapter 2

Sam was curled up on the couch, in Dean’s arms. Dean placed kisses on Sam’s head, hand stroking Sam’s stomach. 

“Daddy?” Sam whispered.

“Yes, princess.”

“Do you think I’m pretty like this?”

“Oh sweetheart. I think you look absolutely beautiful like this.” 

“What’s wrong with me?” Sam whimpered and Dean pulled him close.

“Sammy, we have had a rough life. Our life is fucked up. What we do, what we’ve seen. No one should ever have to see that. Nothing is wrong with you princess. You’re my good girl.” Dean kissed Sam’s forehead. 

Later that night, Sam was getting ready for bed.

“Mommy, can I go to bed with my belly?” Sam asked.

“No, sweetie. That is not healthy.” Castiel said kissing Sam’s lips. 

“Come on, princess. Let’s release you.” Dean soothed.

“Daddy, can I do this again tomorrow?” 

“Princess. We will do it once a week.”

The boys got Sam naked. They washed off his make-up and led him to the shower. Castiel kissed Sam’s stomach and then Dean. Dean put latex gloves on and removed the anal plug. 

Once everything was released, Sam was dressed in his nightgown and stockings. Dean pulled his brother close.

“You’re such a pretty girl” he whispered.

A week later Castiel and Dean woke up and looked at their sleeping girl. 

“What a pretty girl we have” Castiel whispered, stroking Sam’s hair. 

“I know.” Dean smiled, holding Sam’s hand. “Sammy is so perfect. Once our girl is pretty and pregnant, you’re going to be a good boy.”

“Yes sir.”

When Sam was awake they got him ready for the inflation and once his stomach was swollen, they plugged him up and got him dressed. Both new were naked, Castiel had the cock cage on.  
“Look at you, princess.” Dean smiled, kissing Sam’s stomach and kissed. “So pretty.” 

Dean sat down and Castiel crawled under the table to warm Dean’s cock. Dean pulled Sam close and rubbed his stomach. 

“Daddy, do you like it?” Sam whimpered.

“Yeah sweetheart. I love it.” 

“Nn” Castiel gasped a little. Dean had started peeing and didn’t warn him. 

“Drink it all, baby boy” Dean said. “Dance for me” Dean said slapping Sam on the butt.

“Whatever pleases you daddy” Sam said and started to dance. 

“Good girl”

“Mmmm. Look at you, swollen belly. Princess, we love you. You make us proud.” 

“Spank me daddy. Spank me, please!” Sam begged.

“I will, once mommy is done warming my cock.”


	3. Chapter 3

Dean had Castiel still naked, but took the cock cage off. That way he was still his good boy, but Sam had both his doms. Dean walked over to Sam and kissed his lips. He grabbed latex gloves and pulled Sam’s cock out of his panties and undid the cage. Sam gasped.

“Princess, after your spanking, mommy and daddy are going to play with your clit.” He said placing the cage down and slipping Sam’s cock back in. Dean placed to gloved hands on Sam’s inflated belly and placed a kiss. “So beautiful. Now, hands on the chair and bend over, sweetheart.”

“Yes daddy” Sam bent over. “Are you going to keep the gloves on?”

“Yes, princess.” Dean started spanking Sam with one hand and rubbing his stomach with the other. “You’re a good girl, Sammy. What a good princess you are for mommy and daddy. You look really pretty with your belly all swollen. You like that? You like looking pregnant? You are so beautiful. You’re such pretty girl” 

Castiel walked back in and Dean reached a hand down Sam’s panties and started stroking his cock.

“Mmm, daddy, that feels good.” He moaned.

“Yeah, you like when daddy plays with your clit?” Dean whispered.

Dean pulled Sam’s panties down and led him to the bed and laid him down on his back. Castiel came over and pulled down Sam’s bra and started sucking on his nipple. Dean started to stroke Sam’s cock.

“You like when mommy sucks on your titties?” 

“Yes. Mmm, mommy, that feels so good.” 

“Going to be a good girl for daddy and cum on your pretty stomach?” Castiel asked kissing up Sam’s neck. 

“Ye-yes mommy”

Dean squeezed Sam’s balls, listening to his girl moan was amazing. Sam fisted the sheets and Dean made him cum all over his stomach. Both men watched as Sam started to also pee on himself. Sam groaned and Castiel licked his lips, looking at Dean.

“Be a good boy and clean that up.” Dean said.

Dean took off his gloves and Castiel looked at Sam’s stomach with his cum and piss. He stuck his tongue out and started to lick Sam clean. Sam was panting and Dean at by his head and stroked his hair.

“Mommy’s getting you all nice and clean.” Dean whispered. “You’re our good girl, Sammy” 

The boys got Sam stripped and now all three naked men entered the shower. Sam’s makeup started to run, but he didn’t care. Dean washed his hair, massaging his head. Castiel properly cleaned Sam’s stomach. 

“Gonna have you release the water then I’m going to finger your pussy. How does that sound princess?” Dean whispered.

“Yes, daddy. Please. Please. Finger my pussy, l want to be a good girl.”

Was Sam released the inflation Castiel and Dean dried him off and the cock cage was put back on both Sam and Castiel. Dean placed latex gloves on. Sam was lying on his back again. 

“Be a good boy and kneel” Dean instructed to Castiel and he did. “Good boy.”

Dean brushed two fingers against Castiel’s lips and he parted his mouth and started sucing.

“Daddy, please” Sam begged.

“Just getting my fingers nice and slick, princess.” Dean moved his fingers in and out of Castiel’s mouth. 

He then pulled his fingers out and rubbed one on Sam’s hole. He slide one and then the other in. He worked them in and out.

“There’s a good girl.” He cooed. “I have to pee.” Castiel moved between the bed and Dean, wrapping his mouth around Dean’s cock and Dean peed.

“Oh, please! Rub my g-spot.” Sam whined and Castiel felt Dean’s cock twitch in his mouth.

“Mm, love when you ask princess”


	4. Chapter 4

Sam lowered himself on Dean’s cock and started to ride him.

“Mmm, you like that sweetheart? You like daddy’s cock buried in your pussy?”

“Mmm, daddy, it feels sooooo good” Sam said bucking his hips.

Castiel came up behind Sam and started kissing his neck. He rubbed a latex gloved hand on Sam’s nipple and slid it down his chest.

“Going to rub your clit.” Castiel whispered in his ear. “Love watching you ride daddy’s cock.” Castiel stroked Sam’s cock and it twitched.

“Mommy, please! Please!” Sam begged.

Dean reached his hand around spanked Sam’s ass.

“You’re a good girl for us.” Dean said in a low voice. He gave another spank when Castiel pumped Sam’s cock. Sam leaned his head back and to the side and Castiel kissed him. “Mmm, you look beautiful princess with your lipstick smudge. Castiel circled Sam’s tip. Sam audibly gasped.

“Just like that baby girl. You like when mommy rubs your clit while daddy’s in your pussy?”

“Uuhhh” Sam groans. “Don’t stop.”

Dean grips Sam’s hips and jerks his up. With Dean’s grunts and Sam’s moans Castiel was in his own heaven. 

“Fill my pussy daddy” Sam begged.

“You got it princess.” 

A few more pumps and Sam came over Dean’s chest. Sam felt Dean fill him up. Castiel helped Sam off of Dean and plugged him up. Dean pulled Sam close to him while Castiel licked Sam’s cum off of Dean’s chest.

“Mommy, you didn’t cum.” Sam whispered.

“No baby girl, I didn’t need to.” Castiel said. 

A month later Dean and Castiel were shocked to see Sam walk in with his normal clothes on. 

“What’s going on?” Dean asked curious.

“Do we have a case?” Castiel asked. Sam shook his head.

“It’s been a year now. I have been the prettiest princess in the whole world. You and Castiel have made me incredibly happy. I am happy. I was so broken from our past, I’ve hidden that side of me until you let me be a girl, Dean. I just. I’m not fixed, but I’m not broken anymore. I still want to be your princess and baby girl sometimes. Hell, maybe even for a month. But…I’m okay. I can be Sam. I’m healing.” 

Both men got up and kissed Sam, holding him tight.

“I love you, mommy. Daddy.” Sam whispered.

“We love you too, princess.” Dean whispered.

**Notes for the Chapter:**

> Thank you for coming on this wild ride with me.
> 
> Stay tuned for another story I'm writing. 
> 
> I loved writing this series. Much love for all your comments and support.


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